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Compound Detail

CHEMBL253152

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COc1cc([C@@H]2CC(=O)c3c(cc(O)c(C/C=C(\C)CCC=C(C)C)c3O)O2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253152
Phase Preclinical
Structure Type MOL
InChI Key PMKNILHJZILHLN-AGBQBWRISA-N
5
Targets
10
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

438.5
MW (Da)
5.75
ALogP
6
HBA
3
HBD
96.2
PSA (Ų)
0.48
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H30O6
MW 438.52
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness 2.20

Activity Summary

IC50 5 meas. best 5.11
Ki 4 meas. best 5.37
EC50 1 meas. best 5.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neutrophil elastase
CHEMBL248
 Ki 5.37 5.37 4300.0 1
Unchecked
CHEMBL612545
 Ki 5.15 5.15 7100.0 1
Neutrophil elastase
CHEMBL248
 IC50 5.11 5.11 7800.0 1
HeLa
CHEMBL399
 EC50 5.04 5.04 9200.0 1
Unchecked
CHEMBL612545
 IC50 4.88 4.88 13200.0 1
Butyrylcholinesterase
CHEMBL5077
 Ki 4.63 4.63 23600.0 1
Butyrylcholinesterase
CHEMBL5077
 IC50 4.61 4.61 24500.0 1
ADMET
CHEMBL612558
 IC50 4.52 4.52 30200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neutrophil elastase Ki = 4300.0 nM 5.37 Noncompetitive inhibition of human neutrophil elastase using varying levels of M... 28968119
Unchecked Ki = 7100.0 nM 5.15 Mixed-type of inhibition of SARS coronavirus papain-like protease (1541 to 1855 ... 23623680
Neutrophil elastase IC50 = 7800.0 nM 5.11 Inhibition of human neutrophil elastase using MeOSuc-AAPV-pNA as substrate measu... 28968119
HeLa EC50 = 9200.0 nM 5.04 Cytotoxicity against human HeLa cells assessed as viable cells after 72 hrs by c... 20192247
Unchecked IC50 = 13200.0 nM 4.88 Inhibition of SARS coronavirus papain-like protease (1541 to 1855 amino acids) e... 23623680
Butyrylcholinesterase Ki = 23600.0 nM 4.63 Mixed type inhibition of equine BChE using butyrylthiocholine iodide as substrat... 22445674
Butyrylcholinesterase IC50 = 24500.0 nM 4.61 Inhibition of equine BChE assessed as butyrylthiocholine iodide hydrolysis after... 22445674
ADMET IC50 = 30200.0 nM 4.52 Cytotoxicity against rat WB344 cells after 24 hrs 17625893

Literature References

PubMed DOI Target Context # Activities
25735399 10.1021/acs.jnatprod.5b00005 NON-PROTEIN TARGET 5
22445674 10.1016/j.bmc.2012.02.044 Acetylcholinesterase 4
17625893 10.1021/np070063w ADMET 4
23623680 10.1016/j.bmc.2013.03.027 Unchecked 3
22445674 10.1016/j.bmc.2012.02.044 Butyrylcholinesterase 2
25735399 10.1021/acs.jnatprod.5b00005 THP-1 2
28968119 10.1021/acs.jnatprod.7b00325 Neutrophil elastase 2
18293924 10.1021/np070446u Staphylococcus aureus 1
20192247 10.1021/np900681y U-266 1
20192247 10.1021/np900681y RPMI-8226 1
20192247 10.1021/np900681y CCRF-CEM 1
20192247 10.1021/np900681y MCF7 1
18293924 10.1021/np070446u Staphylococcus epidermidis 1
18293924 10.1021/np070446u Enterococcus faecalis 1
18293924 10.1021/np070446u Bacillus subtilis 1
18293924 10.1021/np070446u Bacillus cereus 1
18293924 10.1021/np070446u Candida albicans 1
18293924 10.1021/np070446u Salmonella enteritidis 1
18293924 10.1021/np070446u Pseudomonas aeruginosa 1
18293924 10.1021/np070446u Escherichia coli 1

Data from ChEMBL 36 via Core Engine